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I've been trying to configure a VPN connection between a server running on Xubuntu 14.04, and the client running on Mac OSX Yosemite with no luck. I'm trying to make the connection with Tunnelblick. My Firewall LOG has no relevant information to post. I have opened ports 1194, 443, and 943 for the Mac. I can't quite seem to crack the problem. I will appreciate all help, I don't want to be defeated by this.

Here is the SERVER.CONF:

mode server  
local 192.168.1.XXX #ip of your openvpn server  
port 1194  
proto udp  
dev tun  
ca ca.crt  
cert reinhardtserver.crt  
cert reinhardtserver.key  
dh dh2048.pem  
server 10.8.0.0 255.255.255.0  
ifconfig 10.8.0.1 255.255.255.0  
push "dhcp-option DOMAIN coryreinhardt.com"  
push "dhcp-option DNS 10.6.11.4"  
ifconfig-pool-persist ipp.txt  
keepalive 10 120  
tls-server  
tls-auth ta.key 0  
comp-lzo  
user nobody  
group nobody  
persist-key  
persist-tun  
status openvpn-status.log  
verb1  
client-to-client   
push "route 192.168.0.0 255.255.255.0"`

CLIENT.CONF:

client  
proto udp  
dev tun  
port 1194  
remote 192.168.1.XXX 1194  
resolv-retry infinite  
nobind  
persist-key  
persist-tun  
;mute-replay-warnings  
tls-client  
ca ca.crt  
cert client1.crt  
key client1.key  
tls-auth ta.key 1  
comp-lzo  
verb 3  

TUNNELBLICK LOG:

2015-08-29 20:40:42 *Tunnelblick: openvpnstart starting OpenVPN
2015-08-29 20:40:42 *Tunnelblick: OS X 10.10.5; Tunnelblick 3.5.3 (build 4270.4371); prior version 3.4.2 (build 4055.4161)
2015-08-29 20:40:42 *Tunnelblick: Attempting connection with server using shadow copy; Set nameserver = 1; monitoring connection
2015-08-29 20:40:42 *Tunnelblick: openvpnstart start server.tblk 1337 1 0 1 0 16688 -ptADGNWradsgnw 2.3.6
2015-08-29 20:40:44 *Tunnelblick: openvpnstart log:
 OpenVPN started successfully. Command used to start OpenVPN (one argument per displayed line):

      /Applications/Tunnelblick.app/Contents/Resources/openvpn/openvpn-2.3.6/openvpn
      --daemon
      --log
      /Library/Application Support/Tunnelblick/Logs/-SUsers-Sreinhardt-SLibrary-SApplication Support-STunnelblick-SConfigurations-Sserver.tblk-SContents-SResources-Sconfig.ovpn.1_0_1_0_16688.1337.openvpn.log
      --cd
      /Library/Application Support/Tunnelblick/Users/reinhardt/server.tblk/Contents/Resources
      --config
      /Library/Application Support/Tunnelblick/Users/reinhardt/server.tblk/Contents/Resources/config.ovpn
      --cd
      /Library/Application Support/Tunnelblick/Users/reinhardt/server.tblk/Contents/Resources
      --management
      127.0.0.1
      1337
      --management-query-passwords
      --management-hold
      --script-security
      2
      --up
      /Applications/Tunnelblick.app/Contents/Resources/client.up.tunnelblick.sh -d -f -m -w -ptADGNWradsgnw
      --down
      /Applications/Tunnelblick.app/Contents/Resources/client.down.tunnelblick.sh -d -f -m -w -ptADGNWradsgnw

2015-08-29 20:40:43 OpenVPN 2.3.6 x86_64-apple-darwin [SSL (OpenSSL)] [LZO] [PKCS11] [MH] [IPv6] built on Jul 10 2015
2015-08-29 20:40:43 library versions: OpenSSL 1.0.1p 9 Jul 2015, LZO 2.08
2015-08-29 20:40:43 MANAGEMENT: TCP Socket listening on [AF_INET]127.0.0.1:1337
2015-08-29 20:40:43 Need hold release from management interface, waiting...
2015-08-29 20:40:44 *Tunnelblick: Established communication with OpenVPN
2015-08-29 20:40:44 MANAGEMENT: Client connected from [AF_INET]127.0.0.1:1337
2015-08-29 20:40:44 MANAGEMENT: CMD 'pid'
2015-08-29 20:40:44 MANAGEMENT: CMD 'state on'
2015-08-29 20:40:44 MANAGEMENT: CMD 'state'
2015-08-29 20:40:44 MANAGEMENT: CMD 'bytecount 1'
2015-08-29 20:40:44 MANAGEMENT: CMD 'hold release'
2015-08-29 20:40:44 WARNING: No server certificate verification method has been enabled.  See http://openvpn.net/howto.html#mitm for more info.
2015-08-29 20:40:44 NOTE: the current --script-security setting may allow this configuration to call user-defined scripts
2015-08-29 20:40:44 Control Channel Authentication: using 'ta.key' as a OpenVPN static key file
2015-08-29 20:40:44 Outgoing Control Channel Authentication: Using 160 bit message hash 'SHA1' for HMAC authentication
2015-08-29 20:40:44 Incoming Control Channel Authentication: Using 160 bit message hash 'SHA1' for HMAC authentication
2015-08-29 20:40:44 Socket Buffers: R=[196724->65536] S=[9216->65536]
2015-08-29 20:40:44 UDPv4 link local: [undef]
2015-08-29 20:40:44 UDPv4 link remote: [AF_INET]192.168.1.236:1194
2015-08-29 20:40:44 MANAGEMENT: >STATE:1440906044,WAIT,,,
2015-08-29 20:41:45 TLS Error: TLS key negotiation failed to occur within 60 seconds (check your network connectivity)
2015-08-29 20:41:45 TLS Error: TLS handshake failed
2015-08-29 20:41:45 SIGUSR1[soft,tls-error] received, process restarting
2015-08-29 20:41:45 MANAGEMENT: >STATE:1440906105,RECONNECTING,tls-error,,
2015-08-29 20:41:45 MANAGEMENT: CMD 'hold release'
2015-08-29 20:41:45 WARNING: No server certificate verification method has been enabled.  See http://openvpn.net/howto.html#mitm for more info.
2015-08-29 20:41:45 NOTE: the current --script-security setting may allow this configuration to call user-defined scripts
2015-08-29 20:41:45 Socket Buffers: R=[196724->65536] S=[9216->65536]
2015-08-29 20:41:45 UDPv4 link local: [undef]
2015-08-29 20:41:45 UDPv4 link remote: [AF_INET]192.168.1.236:1194
2015-08-29 20:41:45 MANAGEMENT: >STATE:1440906105,WAIT,,,
2015-08-29 20:42:46 TLS Error: TLS key negotiation failed to occur within 60 seconds (check your network connectivity)
2015-08-29 20:42:46 TLS Error: TLS handshake failed
2015-08-29 20:42:46 SIGUSR1[soft,tls-error] received, process restarting
2015-08-29 20:42:46 MANAGEMENT: >STATE:1440906166,RECONNECTING,tls-error,,
2015-08-29 20:42:46 MANAGEMENT: CMD 'hold release'
2015-08-29 20:42:46 WARNING: No server certificate verification method has been enabled.  See http://openvpn.net/howto.html#mitm for more info.
2015-08-29 20:42:46 NOTE: the current --script-security setting may allow this configuration to call user-defined scripts
2015-08-29 20:42:46 Socket Buffers: R=[196724->65536] S=[9216->65536]
2015-08-29 20:42:46 UDPv4 link local: [undef]
2015-08-29 20:42:46 UDPv4 link remote: [AF_INET]192.168.1.236:1194
2015-08-29 20:42:46 MANAGEMENT: >STATE:1440906166,WAIT,,,
2015-08-29 20:42:47 *Tunnelblick: Disconnecting; VPN Details… window disconnect button pressed
2015-08-29 20:42:47 *Tunnelblick: Disconnecting using 'kill'
2015-08-29 20:42:47 event_wait : Interrupted system call (code=4)
2015-08-29 20:42:47 SIGTERM[hard,] received, process exiting
2015-08-29 20:42:47 MANAGEMENT: >STATE:1440906167,EXITING,SIGTERM,,
2015-08-29 20:42:49 *Tunnelblick: No 'post-disconnect.sh' script to execute
2015-08-29 20:42:49 *Tunnelblick: Expected disconnection occurred.

and here is an ifconfig from Xubuntu :

root@reinhardt:/etc/openvpn# ifconfig
eth0      Link encap:Ethernet  HWaddr 00:26:22:1e:c6:58  
      UP BROADCAST MULTICAST  MTU:1500  Metric:1
      RX packets:0 errors:0 dropped:0 overruns:0 frame:0
      TX packets:0 errors:0 dropped:0 overruns:0 carrier:0
      collisions:0 txqueuelen:1000 
      RX bytes:0 (0.0 B)  TX bytes:0 (0.0 B)

lo        Link encap:Local Loopback  
      inet addr:127.0.X.X  Mask:255.0.0.0
      inet6 addr: ::1/128 Scope:Host
      UP LOOPBACK RUNNING  MTU:65536  Metric:1
      RX packets:3290 errors:0 dropped:0 overruns:0 frame:0
      TX packets:3290 errors:0 dropped:0 overruns:0 carrier:0
      collisions:0 txqueuelen:0 
      RX bytes:308681 (308.6 KB)  TX bytes:308681 (308.6 KB)

wlan0     Link encap:Ethernet  HWaddr 00:26:5e:69:27:0d  
      inet addr:192.168.1.XXX  Bcast:192.168.1.XXX  Mask:255.255.XXX.X
      inet6 addr: 2602:30a:2e8c:9a20:5c1a:7c51:8bcc:8720/64 Scope:Global
      inet6 addr: 2602:30a:2e8c:9a20:226:5eff:fe69:270d/64 Scope:Global
      inet6 addr: fe80::226:5eff:fe69:270d/64 Scope:Link
      UP BROADCAST RUNNING MULTICAST  MTU:1500  Metric:1
      RX packets:41514 errors:0 dropped:0 overruns:0 frame:0
      TX packets:16935 errors:0 dropped:0 overruns:0 carrier:0
      collisions:0 txqueuelen:1000 
      RX bytes:11636203 (11.6 MB)  TX bytes:2545476 (2.5 MB)
1
  • found a solution to this?
    – lukik
    Dec 31, 2015 at 3:36

0

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